[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]=[N+:11]=[N-:12])=[CH:4][CH:3]=1A mixture of 4-bromobenzyl bromide (54) and sodium azide (2.0 equiv.) in DMF was stirred at 50° C. for 3 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined organic extract was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography to yield 55 as colorless oil in 92% yield.
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